Great Barrington holiday homes
We found 947 holiday rentals — enter your dates for availability
Select the perfect holiday rental within easy reach of Great Barrington, MA (GBR-Walter J. Koladza). Holiday rentals offer the best amenities for your family, friends or furry companion, such as parking and a washer and dryer. You'll be sure to find a property to rent for everyone's needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Great Barrington, MA (GBR-Walter J. Koladza)
Showing deals for:1 Aug - 8 Aug
Image gallery for Modern, private, spacious vacation home, deck, mountain views, 5 mi to Catamount
1010 out of 10 rating
Exceptional
(10 reviews)
Modern, private, spacious vacation home, deck, mountain views, 5 mi to Catamount
Hillsdale, NY
8% off
Price is NZ$8,905
NZ$8,905
NZ$1,272 per night
includes taxes & fees
Image gallery for Private Access To Laurel Lake, Enjoy Lake Life
1010 out of 10 rating
Exceptional
(14 reviews)
Private Access To Laurel Lake, Enjoy Lake Life
Lenox, Massachusetts
16% off
Price is NZ$19,004
NZ$19,004
NZ$2,715 per night
includes taxes & fees
Image gallery for Taghkanic Glass House
1010 out of 10 rating
Exceptional
(6 reviews)
Taghkanic Glass House
Hudson, NY
8% off
Price is NZ$58,263
NZ$58,263
NZ$8,323 per night
includes taxes & fees
Image gallery for Ashintully Cottage in spectacular setting
1010 out of 10 rating
Exceptional
(33 reviews)
Ashintully Cottage in spectacular setting
Lee, MA
17% off
Price is NZ$4,407
NZ$4,407
NZ$630 per night
includes taxes & fees
Image gallery for Views of Catamount! Tanglewood, Skiing, Bash Bish Falls, Barn At Liberty Farms!
1010 out of 10 rating
Exceptional
(43 reviews)
Views of Catamount! Tanglewood, Skiing, Bash Bish Falls, Barn At Liberty Farms!
Hillsdale, NY
8% off
Price is NZ$13,423
NZ$13,423
NZ$1,918 per night
includes taxes & fees
Image gallery for Salisbury Cottage Retreat
1010 out of 10 rating
Exceptional
(9 reviews)
Salisbury Cottage Retreat
Salisbury, CT
16% off
Price is NZ$3,099
NZ$3,099
NZ$443 per night
includes taxes & fees
Image gallery for Waterfront Escape +dock +kayaks +firepit +fireplace +games
9.89.8 out of 10 rating
Exceptional
(10 reviews)
Waterfront Escape +dock +kayaks +firepit +fireplace +games
Copake, NY
8% off
Price is NZ$5,316
NZ$5,316
NZ$759 per night
includes taxes & fees
Image gallery for Newly renovated charming home , Brand new chefs kitchen very comfortable home .
1010 out of 10 rating
Exceptional
(8 reviews)
Newly renovated charming home , Brand new chefs kitchen very comfortable home .
Lakeville, CT
12% off
Price is NZ$4,819
NZ$4,819
NZ$688 per night
includes taxes & fees
Image gallery for Copake Lake home near cultural attractions Of The Berkshires
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Copake Lake home near cultural attractions Of The Berkshires
Hillsdale, NY
8% off
Price is NZ$3,906
NZ$3,906
NZ$558 per night
includes taxes & fees
Image gallery for Serene, stylish cottage - close to Hudson - New Listing
1010 out of 10 rating
Exceptional
(29 reviews)
Serene, stylish cottage - close to Hudson - New Listing
Hudson, NY
8% off
Price is NZ$1,917
NZ$1,917
NZ$274 per night
includes taxes & fees
Image gallery for Modern Glass House designed by renowned architect Thomas Phifer
9.09.0 out of 10 rating
Wonderful
(6 reviews)
Modern Glass House designed by renowned architect Thomas Phifer
Hudson, NY
8% off
Price is NZ$7,647
NZ$7,647
NZ$1,092 per night
includes taxes & fees
Image gallery for Berkshire Lake at the Pillow, and EV!
9.49.4 out of 10 rating
Exceptional
(15 reviews)
Berkshire Lake at the Pillow, and EV!
Lee, MA
8% off
Price is NZ$5,204
NZ$5,204
NZ$743 per night
includes taxes & fees
Image gallery for Cozy Cabin in the Berkshires
1010 out of 10 rating
Exceptional
(16 reviews)
Cozy Cabin in the Berkshires
Sandisfield, MA
12% off
Price is NZ$3,158
NZ$3,158
NZ$451 per night
includes taxes & fees
Image gallery for Guesthouse Cabin vacation rentals in Berkshire County
1010 out of 10 rating
Exceptional
(5 reviews)
Guesthouse Cabin vacation rentals in Berkshire County
Sheffield, MA
8% off
Price is NZ$8,650
NZ$8,650
NZ$1,236 per night
includes taxes & fees
Image gallery for Charming Cottage, New Marlborough Village Green in the Berkshires
1010 out of 10 rating
Exceptional
(62 reviews)
Charming Cottage, New Marlborough Village Green in the Berkshires
Great Barrington, MA
8% off
Price is NZ$3,102
NZ$3,102
NZ$443 per night
includes taxes & fees
Image gallery for Berkshire Rural Retreat
1010 out of 10 rating
Exceptional
(21 reviews)
Berkshire Rural Retreat
Canaan, NY
8% off
Price is NZ$5,745
NZ$5,745
NZ$821 per night
includes taxes & fees
Image gallery for Perfect Vacation Get Away - Historical New Marlborough
9.49.4 out of 10 rating
Exceptional
(54 reviews)
Perfect Vacation Get Away - Historical New Marlborough
Great Barrington, MA
12% off
Price is NZ$2,392
NZ$2,392
NZ$342 per night
includes taxes & fees
Image gallery for Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
9.89.8 out of 10 rating
Exceptional
(9 reviews)
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
South Egremont, MA
8% off
Price is NZ$5,169
NZ$5,169
NZ$738 per night
includes taxes & fees
Image gallery for Beautifully Restored, Secluded Farmhouse
1010 out of 10 rating
Exceptional
(23 reviews)
Beautifully Restored, Secluded Farmhouse
Hillsdale, NY
7% off
Price is NZ$6,495
NZ$6,495
NZ$928 per night
includes taxes & fees
Image gallery for Charming cedar shingle cottage
9.89.8 out of 10 rating
Exceptional
(54 reviews)
Charming cedar shingle cottage
Otis, MA
6% off
Price is NZ$3,853
NZ$3,853
NZ$550 per night
includes taxes & fees
Image gallery for Cozy Cabin on Lake Mahkeenac
8.88.8 out of 10 rating
Excellent
(10 reviews)
Cozy Cabin on Lake Mahkeenac
West Stockbridge, MA
8% off
Price is NZ$4,130
NZ$4,130
NZ$590 per night
includes taxes & fees
Image gallery for Chester by AvantStay | Amazing Views, Secluded Home, A True City Escape!
9.29.2 out of 10 rating
Wonderful
(7 reviews)
Chester by AvantStay | Amazing Views, Secluded Home, A True City Escape!
Austerlitz, NY
9% off
Price is NZ$12,756
NZ$12,756
NZ$1,822 per night
includes taxes & fees
Image gallery for Relaxing retreat in the Berkshires! Perfect for outdoor enthusiast!
9.89.8 out of 10 rating
Exceptional
(14 reviews)
Relaxing retreat in the Berkshires! Perfect for outdoor enthusiast!
Sandisfield, MA
8% off
Price is NZ$2,698
NZ$2,698
NZ$385 per night
includes taxes & fees
Image gallery for Private apartment in beautiful country barn
1010 out of 10 rating
Exceptional
(18 reviews)
Private apartment in beautiful country barn
Richmond, MA
12% off
Price is NZ$2,612
NZ$2,612
NZ$373 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Great Barrington
Short Drive to Norman Rockwell Museum! Indoor and Outdoor Pool, Free Parking!
Sleeps 6 · 2 bedrooms · 2 bathrooms
8.88.8 out of 10
Excellentexcellent
6 reviews(6 reviews)
Hudson Valley private 70's-style cabin on five acres, five minutes to town!
Sleeps 6 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
Guesthouse Cabin vacation rentals in Berkshire County
Sleeps 12 · 4 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
5 reviews(5 reviews)
Restored historic farmhouse on 25 private acres
Sleeps 6 · 3 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
The City Farmers Upstate. 15 min from Hudson. Family friendly. Hot tub and Sauna
Sleeps 12 · 5 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
13 reviews(13 reviews)
The Library Retreat: 3 Building Estate w/Pool+Pond
Sleeps 12 · 7 bedrooms · 5+ bathrooms
1010 out of 10
Exceptionalexceptional
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value